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A new carbohydrate-based synthetic approach to trichothecenes. Synthesis of a bicyclic BC core of verrucarol from d-galactose

โœ Scribed by Mikhail S Ermolenko


Book ID
104231422
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
95 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


An advanced bicyclic BC intermediate towards the total synthesis of verrucarol has been prepared from D-galactose via an intramolecular aldehyde-allylstannane reaction.


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The functionalized tricyclic framework (XI) of the diterpene forskolin is synthesized by an intramolecular Diels-Alder reaction of the dienyne (VII), which is obtained by stereoselective introduction of the C side chains at C-1 and C-2 of tri-O-acetyl-D-galactal (I) via C-Ferrier and Claisen-Ireland